Over the past decade, state officials have pursued a variety of strategies to protect and expand health insurance coverage for their residents. This article examines the course of action in Maryland, where new initiatives were shaped around the state's unique hospital payment system and its reimbursement of uncompensated care, an evolving Medicaid and children's health program, and regulation of the small group health insurance market. Several important patterns emerge from the Maryland experience. First, even the most incremental initiatives—programs intended to aid a few thousand beneficiaries—bring into play the very issues that hamper comprehensive reforms: who is deserving of mutual aid and what is the proper role of government versus private entities in administering that aid. In Maryland,these issues generate conflict not only between Democrats and Republicans but also urban and rural interests. Second, all of the important reforms of the past decade were undertaken primarily in reaction to federal policy initiatives. Contrary to rhetoric lauding states as the “laboratories of democracy,” the political impetus for reform and basic policy options emerge from interaction between federal and state debates. Third, even with budget surpluses and Democrats in control of the governorship and legislature,Maryland did not move aggressively toward universal health insurance. Now,with a much weaker economy and a new, Republican governor, the primary challenge will be to prevent further erosion of insurance coverage. The Maryland experience reiterates that each step toward greater health security,no matter how small, is a major technical and political challenge and that it will be difficult if not impossible to rely on states to secure coverage for all Americans in the foreseeable future.